The closest we ever got was a pretty good but flawed and now old Gangsters: Organized Crime (the "sequel" was a turd).

A game where a crime boss has to hire and organize his henchmen and assign them tasks and crimes to commit, set up and maintain illegal businesses, manage his legal affairs (lawyer, accountant, bribing officials, managing the police, dodging the FBI, keeping the heat down to avoid serious legal problems, occasional assassinations, etc), purchasing legal businesses as either fronts or as assets to either cool off some heat or simply diversify, manage squealers and extortion rackets, etc. And it would be extra fun if it were set in, say, 1980 when the drug cartels blew up and started to cross horns with the traditional syndicates/mafia/etc.

I've thought about your idea for a while, and couldn't agree more that it would be an awesome game, using a WMMA3 type engine.

*Companies could be Families or Gangs, Italian, Sicilian, Irish, Eastern European, Asian, whatever; they could takeover and control weaker Families; Families could be at war
*Fighters could be the available pool of crooks - they could start as associates and as they advanced in ''notoriety'' they could become ''Made Men'' (exclusive deals). Specialisations could include extortion, thuggery, assassination/murder, safe-breaking, bomb-making, gambling, pimping, racketeering, bootlegging, smuggling, , intimidation, bribery, laundering, hijacking. Crooks who are killed, executed or jailed for life would become regens, or else they could do a few years in prison and be released. Maybe even prison-breaks could be implemented.
*Regions could be either as they are or lesser territories like Brooklyn, Queens, South LA etc ''Popularity'' would equate to ''Influence'' and have a direct bearing on criminal income
*The match screen could be a PBP of operations or criminal enterprises as they take place, taking the player in detail through a successful or botched operation. Player stats would of course have a direct bearing on discovery, interruption etc. You'd use your best men for the difficult jobs, and lesser associates for easier jobs and to build up their stats. It would certainly be exciting!
*TV/PPV type interactions would be analagous to interactions with government bodies, like police/FBI/government figures. They could involve bribery and payoffs.

This idea for a game seems much darker or gritty than the usual GDS production, however I think it would be awesome. Imagine a database of the US in the 1920s-1940s for example, during Prohibition with the likes of Al Capone & Co!!!

Location: When i look at the television i wanna see me, stare right back at me!

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I like this - I actually like the idea of a game based around Breaking Bad. Where you literally start your career as a small time guy and work your way up to a big time player. There could be multiple paths as well. You could have a character where if you build their physical stats they start of doing protection gigs, or if you have high stealth they are more cat burglars, pickpockets, or if they have brains they make drugs etc. So much potential in a simulated crime game.